Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin
7,8-Dihydrobiopterin (H2Bip) and 7,8-dihydroneopterin (H2Nep) belong to a class of heterocyclic compounds present in a wide range of living systems. H2Bip accumulates in the skin of patients suffering from vitiligo, whereas H2Nep is secreted by human macrophages when the cellular immune system is ac...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_1474905X_v11_n6_p979_Vignoni |
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todo:paper_1474905X_v11_n6_p979_Vignoni2023-10-03T16:18:16Z Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin Vignoni, M. Lorente, C. Cabrerizo, F.M. Erra-Balsells, R. Oliveros, E. Thomas, A.H. 7,8 dihydroneopterin 7,8-dihydrobiopterin 7,8-dihydroneopterin biopterin dihydrobiopterin drug derivative neopterin article chemistry dimerization electrospray mass spectrometry high performance liquid chromatography human isomerism macrophage metabolism nuclear magnetic resonance spectroscopy photolysis temperature ultraviolet radiation Biopterin Chromatography, High Pressure Liquid Dimerization Humans Isomerism Macrophages Magnetic Resonance Spectroscopy Neopterin Photolysis Spectrometry, Mass, Electrospray Ionization Temperature Ultraviolet Rays 7,8-Dihydrobiopterin (H2Bip) and 7,8-dihydroneopterin (H2Nep) belong to a class of heterocyclic compounds present in a wide range of living systems. H2Bip accumulates in the skin of patients suffering from vitiligo, whereas H2Nep is secreted by human macrophages when the cellular immune system is activated. We have investigated the photochemical reactivity of both compounds upon UV-A irradiation (320-400 nm), the chemical structures of the products and their thermal stability. The study was performed in neutral aqueous solutions. The reactions were followed by UV/Visible spectrophotometry and HPLC and the products were analyzed by means of electrospray ionization mass spectrometry and 1H-NMR. Excitation of H2Bip and H2Nep leads to the formation, in each case, of two main isomeric dimers. The latter compounds undergo a thermal process that may consist in a retro [2 + 2]-cycloaddition and hydrolysis to yield the reactant (H2Bip or H2Nep) and a product that has incorporated a molecule of H2O. © The Royal Society of Chemistry and Owner Societies 2012. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1474905X_v11_n6_p979_Vignoni |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
7,8 dihydroneopterin 7,8-dihydrobiopterin 7,8-dihydroneopterin biopterin dihydrobiopterin drug derivative neopterin article chemistry dimerization electrospray mass spectrometry high performance liquid chromatography human isomerism macrophage metabolism nuclear magnetic resonance spectroscopy photolysis temperature ultraviolet radiation Biopterin Chromatography, High Pressure Liquid Dimerization Humans Isomerism Macrophages Magnetic Resonance Spectroscopy Neopterin Photolysis Spectrometry, Mass, Electrospray Ionization Temperature Ultraviolet Rays |
| spellingShingle |
7,8 dihydroneopterin 7,8-dihydrobiopterin 7,8-dihydroneopterin biopterin dihydrobiopterin drug derivative neopterin article chemistry dimerization electrospray mass spectrometry high performance liquid chromatography human isomerism macrophage metabolism nuclear magnetic resonance spectroscopy photolysis temperature ultraviolet radiation Biopterin Chromatography, High Pressure Liquid Dimerization Humans Isomerism Macrophages Magnetic Resonance Spectroscopy Neopterin Photolysis Spectrometry, Mass, Electrospray Ionization Temperature Ultraviolet Rays Vignoni, M. Lorente, C. Cabrerizo, F.M. Erra-Balsells, R. Oliveros, E. Thomas, A.H. Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| topic_facet |
7,8 dihydroneopterin 7,8-dihydrobiopterin 7,8-dihydroneopterin biopterin dihydrobiopterin drug derivative neopterin article chemistry dimerization electrospray mass spectrometry high performance liquid chromatography human isomerism macrophage metabolism nuclear magnetic resonance spectroscopy photolysis temperature ultraviolet radiation Biopterin Chromatography, High Pressure Liquid Dimerization Humans Isomerism Macrophages Magnetic Resonance Spectroscopy Neopterin Photolysis Spectrometry, Mass, Electrospray Ionization Temperature Ultraviolet Rays |
| description |
7,8-Dihydrobiopterin (H2Bip) and 7,8-dihydroneopterin (H2Nep) belong to a class of heterocyclic compounds present in a wide range of living systems. H2Bip accumulates in the skin of patients suffering from vitiligo, whereas H2Nep is secreted by human macrophages when the cellular immune system is activated. We have investigated the photochemical reactivity of both compounds upon UV-A irradiation (320-400 nm), the chemical structures of the products and their thermal stability. The study was performed in neutral aqueous solutions. The reactions were followed by UV/Visible spectrophotometry and HPLC and the products were analyzed by means of electrospray ionization mass spectrometry and 1H-NMR. Excitation of H2Bip and H2Nep leads to the formation, in each case, of two main isomeric dimers. The latter compounds undergo a thermal process that may consist in a retro [2 + 2]-cycloaddition and hydrolysis to yield the reactant (H2Bip or H2Nep) and a product that has incorporated a molecule of H2O. © The Royal Society of Chemistry and Owner Societies 2012. |
| format |
JOUR |
| author |
Vignoni, M. Lorente, C. Cabrerizo, F.M. Erra-Balsells, R. Oliveros, E. Thomas, A.H. |
| author_facet |
Vignoni, M. Lorente, C. Cabrerizo, F.M. Erra-Balsells, R. Oliveros, E. Thomas, A.H. |
| author_sort |
Vignoni, M. |
| title |
Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| title_short |
Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| title_full |
Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| title_fullStr |
Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| title_full_unstemmed |
Characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| title_sort |
characterization and reactivity of photodimers of dihydroneopterin and dihydrobiopterin |
| url |
http://hdl.handle.net/20.500.12110/paper_1474905X_v11_n6_p979_Vignoni |
| work_keys_str_mv |
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